Holiday rentals with a pool in Palm Harbor

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

5 out of 5 average rating, 123 reviews

Coastal Escape: heated saltwater pool & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

4.97 out of 5 average rating, 132 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Guest house in Palm Harbor

A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.

4.86 out of 5 average rating, 160 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

4.88 out of 5 average rating, 103 reviews

A well-maintained pool area features two inviting swimming pools, surrounded by lounge chairs. A hot tub is positioned nearby, with palm trees visible in the background. Outdoor lighting enhances the space, creating a relaxing atmosphere for guests to enjoy.

Apartment in Dunedin

Fall special rate ! Pool, hot tub at Beso Resort !

Plan your unforgettable stay at this 1 bedroom condo at Beso ( not a studio) with 2 Balconies for your morning coffee or beautiful sunsets The location is perfect to walk to town where you’ll find many Quaint shops, restaurants and Breweries Free Wi-fi Free parking Only 10 min to honeymoon island and the ferry to Caladesi Island 15 minutes to Clearwater Beach 2 salt water Pools and a hot tub Marker 8 Tiki Bar and restaurant 28 mile trail across St. Bicycle rental through the office for a fee

The outdoor area features a heated pool with crystal-clear water, surrounded by a screened lanai. Comfortable lounge chairs are placed nearby, providing ideal spots for relaxation. Tropical plants enhance the space, framing a serene environment perfect for swimming and sunbathing.

4.9 out of 5 average rating, 124 reviews

Heated Pool, 10 min to Beach, Close to Restaurants

Welcome to Turtle House! Perfectly situated in the heart of Palm Harbor lies this gem. Enjoy a completely renovated private heated pool, and with a quick and convenient access to US19 enjoy shopping, restaurants or local beaches. Perfect for families, couples, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment and relaxation. 10% discount for Military, First Responders, Teachers, friends and family - book & message me, I'll apply the discount, that's it!

A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.

4.99 out of 5 average rating, 143 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

4.99 out of 5 average rating, 256 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool-All Essentials Provided

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

Guest suite in Tarpon Springs

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

4.96 out of 5 average rating, 134 reviews

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

4.96 out of 5 average rating, 372 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.

4.95 out of 5 average rating, 159 reviews

Tropical Getaway w/Heated Pool & King Beds

Welcome to our sun-kissed getaway in sunny Palm Harbor! You'll find a fully stocked kitchen, a private heated pool, and comfortable accommodations for up to 6 guests. Whether relaxing on one of our award-winning beaches, playing a round of golf, or exploring Tampa Bay's fun spots, there's something for everyone to enjoy. Just a quick note: Because of a family member's allergies, we're not able to allow any animals on the property, including ESAs. Thanks so much for understanding!

A spacious bedroom is equipped with a king-size bed, complemented by nightstands with lamps. A flat-screen smart TV is mounted on the wall. Artwork adorns the walls, and natural light filters through the windows, offering a view of the pool area from the ground floor.

4.94 out of 5 average rating, 117 reviews

By the POOL, Ground floor, King bed, NO PETS

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Walk-in distance to Publix grocery store and nearby restaurants. Location is central with short distance to nearby beaches, attractions and other nearby towns. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport and Disney World This location is loved by “snowbirds”

5 out of 5 average rating, 146 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Popular amenities for Palm Harbor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A screened-in saltwater pool is surrounded by a spacious patio area featuring several lounge chairs. Clear blue water reflects sunlight, while a basketball hoop is positioned above the pool's edge. The serene outdoor space encourages relaxation and leisure.

5 out of 5 average rating, 33 reviews

Paradise Found Honeymoon Beach, Heated Salt Pool

4.97 out of 5 average rating, 159 reviews

A cozy outdoor fire-pit area is surrounded by colorful seating. Decorative stones cover the ground, leading to a grill and the inviting glow of flames. A pool and shaded area can be seen in the background, set against a twilight sky.

Home in Clearwater

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

A modern single-story house is set on a manicured lawn, featuring a paved driveway and a two-car garage. In front, two colorful chairs are positioned under the shade of mature trees, enhancing the welcoming entrance of the home.

4.8 out of 5 average rating, 35 reviews

Newly Remodeled*3 Beds*Pool*Game Room*10minBeach

4.91 out of 5 average rating, 53 reviews

Private Pool! Tropical Beaches! Palm Harbor, FL

4.9 out of 5 average rating, 113 reviews

Home in Clearwater

Clearwater Escape • Pool • Spa • Pet Friendly

4.95 out of 5 average rating, 150 reviews

A spacious primary bedroom features a comfortable bed with neutral bedding and softly colored walls. Light enters through large windows adorned with sheer curtains, creating a bright and airy space. A modern lamp provides additional lighting beside the bed.

Home in Dunedin

Dunedin 5 STAR! Heated POOL+10 Mins to Beach

A modern two-story home features a balanced façade with white walls and large arched windows. Lush palm trees and landscaped greenery frame the entrance, creating an inviting approach. The dual garage doors provide additional functionality, complementing the home's contemporary design.

4.98 out of 5 average rating, 60 reviews

Luxury Waterfront w/ Private Heated Pool

5 out of 5 average rating, 14 reviews

A modern kitchen space features deep blue cabinetry and stainless steel appliances. A large island with a white countertop is centered in the room, surrounded by light grey stools. Natural light filters through a nearby glass door, enhancing the bright atmosphere.

Home in Port Richey

HGTV Style Pool House on the Water

Apartment rentals with a pool

4.93 out of 5 average rating, 206 reviews

A comfortable living area features a neutral-colored sofa, a round dining table, and a ceiling fan. Large sliding glass doors provide access to a balcony, allowing natural light to fill the space and offering views of palm trees outside.

Apartment in Tampa

Waterfront Condo - Sunset View of Tampa Bay

Apartment in Clearwater Beach

A cozy sitting area is featured on the private balcony, highlighted by a circular rattan chair adorned with soft cushions. Green plants provide a touch of nature, while water views and boats can be seen beyond the railing, enhancing the relaxing atmosphere.

4.99 out of 5 average rating, 136 reviews

Waterfront Condo | Steps to Clearwater Beach 2King

4.89 out of 5 average rating, 219 reviews

A bright living room features a gray couch with colorful accent pillows, positioned next to a coffee table. Large sliding glass doors open to a view of the patio. A rug with intricate designs lies on the floor, complemented by a cozy accent chair.

Apartment in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

4.96 out of 5 average rating, 103 reviews

A heated swimming pool is surrounded by neatly arranged loungers, with palm trees providing shade. A clear sky and vibrant sunset colors reflect on the water's surface. The pool area is enclosed by a black fence, ensuring a private and relaxing environment.

Apartment in Largo

Boho Beach Condo

A modern living area features a large television mounted on the wall, framed by a stylish red console. Two comfortable chairs and a table are arranged in front of a sliding glass door, which opens to a private balcony with tropical greenery visible outside.

4.95 out of 5 average rating, 146 reviews

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

The heated swimming pool is surrounded by palm trees and lounge chairs, offering a relaxing atmosphere. The pool area features a spacious deck with light-colored paving, while nearby buildings provide a serene backdrop, enhancing the inviting outdoor setting.

4.81 out of 5 average rating, 164 reviews

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

Apartment in Clearwater Beach

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 397 reviews

Amazing views on beachfront

4.98 out of 5 average rating, 239 reviews

An open living area features a modern kitchen with white cabinetry and a large island with bar seating. A comfortable couch is positioned in front of an electric fireplace, accompanied by a coffee table displaying books and a decorative plant. A wall-mounted TV displays a vibrant underwater scene.

Apartment in Seminole

SHEEK and Glam- heated pool Updated! 3 mi to beach

Other holiday rentals with a pool

A modern kitchen is presented with stylish white cabinetry and a spacious concrete countertop. Two pendant lights hang above the bar seating, which features four black chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, providing a well-equipped cooking space.

5 out of 5 average rating, 49 reviews

Wonderful Condo at Avalon - Fully Renovated!

A screened-in outdoor area features a pool and hot tub, surrounded by a spacious deck. Comfortable seating options include lounge chairs and an umbrella-covered table. Large glass doors provide a view into the interior living space, allowing for natural light to flow through.

4.88 out of 5 average rating, 80 reviews

Quiet Oceanside Getaway - PALM HARBOR, FL

A private pool area is presented, featuring a curved, shallow-end pool surrounded by a spacious concrete deck. The home is seen in the background, with large windows and a covered patio that offers additional shaded seating options. Lush greenery borders the area, providing a natural ambiance.

4.83 out of 5 average rating, 12 reviews

Cool Palm Harbor Spot

4.87 out of 5 average rating, 68 reviews

Valencia Manor, your Favorite Florida Pool Home!

4.91 out of 5 average rating, 11 reviews

Townhouse in Clearwater

Clearwater Coastal Oasis - Heated Pool

4.9 out of 5 average rating, 10 reviews

Luxe Retreat Paradise

4.97 out of 5 average rating, 37 reviews

A private pool area is presented with inviting waters and various colorful floaties arranged on the surface. The pool is bordered by a spacious deck, featuring outdoor seating. Views of a serene body of water and lush greenery are visible in the background.

Home in Clearwater

Paradise Point Home in Clearwater-5 miles to beach